Monoazo dyestuffs



Patented Oct. 25, 1938 UNITED=STATES PAT NT. I E

MoNoAz0 DYESTUFFS Richard 'Fleischhauer, Frankfort-on-the Main Fechenheim, Germany, assig'nor' to General w v Aniline iWo'rks, Inc.,' New York,; N. Y., aucor poration of Delaware narrating. Application October 16, 1936 serial No. 105,931. In Germany October :22,

This invention relates to valuable new monoazodyestufis, more particularly to those of the general formula:

| COX (wherein X has the above signification) with 2- aryl-amino-8-naphthol-6-sulfonic acids.

' The diazo components employed for themanufacture of the dyestuffs of this invention may be prepared for example in an analogous manner to the methods described in German Patents No. 152,012 and No. 154,556. Or they may be prepared by starting from nitro-aryl-glycines which are acylated and reduced.

The new dyestuffs yield on animal fibers brown shades of good fastness properties. They are distinguished from similar brown dyestuffs by a very good solubility and partly by a much better fastness to ironing.

9 The following examples illustrate, but do not limit the invention, the parts being by weight.

Example 1 20.8 parts of N-(4-aminophenyl) -N-acetyl-aminc-acetic acid are diazotized in the usual manner 4D and the diazo solution obtained is combined with 35 parts of 2-(4-methoxyphenylamino) -8-naphthol-6-sulfonic acid in the presence of an excess of sodium carbonate. The dyestufi formed of the 45 formula:

COCHa 50 HOaS 5 light and of good levelling power.

3 Claims. (01." 266 921.

When the combination is performed in the presence of another acid-binding agent such as for example sodium bicarbonate dyestuifs are obtained which yield somewhat more reddish brown shades of similar properties.

Instead of the above diazo component there may be used in an analogous manner other similar compounds such as for example:

N- (4-aminophenyl) -N-methoxyacety1-aminoacetic acid, N-(-amiriophenyl) N carbethoxyaminoacetic. acid; N-(4-aminopheny1) -N-chloroacetyl-aminoacetic acid; N-(4-aminophenyl) N-- phenoxyacetyl arninoacetic acid; N-(-4-aminophenyl) -N-benzoyl-aminoacetic acid, N-(4-aminophenyl) -N-hexahydrobenzoylaminoac'etic acid, N-(l-aminophenyl) -N-propionyl-aminoacetic acid, N- (4-amino-2-methylphenyl) -N-acetyl-aminoacetic acid or substituted derivatives thereof.

By employing the corresponding amounts of these diazoi components.instea'diof the above said N- (4 aminophenyl) N acetyl aminoacetic acid brown dyestuffs areobtained of quite analogous properties and partly distinguished by an' increased fastness to light or by deeper brown shades. Thus the dyestufi prepared by starting from N- (-aminophenyl) :N-benzoyl-aminoacetic I acid yields deeper brown shadesthan the dyestuff prepared by starting from N-(4-aminophenyD- N -acetyl-aminoacetic acid.

Example 2 20.8 parts of N-(i-aminophenyl) -N-acetylaminoacetic acid are diazotized in the usual manner and the diazo solution obtained is combined with 35 parts of 2- (4'- methoxy-phenylamino) -8-naphthol-fi-sulfonic acid in the presence of an excess of sodium acetate. The dyestufi" formed is isolated and dried. It forms a dark powder, easily soluble in water, dyeing wool deep violet-tinged brown shades of quite similar properties as the dyestuif obtained according to Example 1, but of a somewhat increased fastness to light.

The diiference between the new product and the dyestufi obtained according to Example 1 seems to be caused by the fact that a little amount of another dyestufi is produced beside the dyestufi the formula of which is given in Example 1, whereby the combination probably takes place in the 1-position of the coupling component. When the amount of the sodium acetate employed is varied, more or less of the byproduct is formed and the properties of the dyestufl obtained may be altered thereby.

Instead of the above coupling component there may also be employed in the foregoing examples 2-arylamino-8-naphthol-6-sulionic acids which may contain further substituents in their aryl radicle. Such coupling components are for example:

Z-phenylamino 8-naphthol-6-sulfonic acid, 2-

(2'- methyl-phenylamino) -8-naphtho1-6-sulfonic acid, 2- (2-methoxy-phenylamino) -8-- naphthol- 6-sulfonic acid, 2-(2',4-dimethoxy-phenylamino) -8-naphthol-6-sulfonic acid, 2-(2,5dimethoxy-phenylamino)-8-naphthol-6 sulfonic acid, 2-(chloro-phenylamino) -8-naphthol 6 sulfonic acids, 2- (sulfo-phenylamino) -8-naphtho1-6-s ulfonic acids, z-(carboxy-phenylamino) 8-naphthol-fi-sulfonic acids.

Ezample b 19.4 parts of N-(4-aminophenyl) -N-.formy1-am inoacetic acid are diazotized in the usual manner and the diazo solution obtained is allowed to run into a solution of 35 parts of 2- (4methoxy-phenylamino) 8enaphthol-fi-sulfonic acid containing an excess of sodium bicarbonate. When the combination is complete the dyestufi formed substantially consisting of a product of the formula:

is isolated by the addition of an acid and of sodium chloride. It is when dry a dark powder. soluble in water, dyeing wool and silk very deep brown shades of good Iastness to ironing and of good levelling power.

I claim:

1. The monoazo dyestufls consisting substantially .0! products of the general formula:

(LO-X H018 wherein X standsfor a member selected from the group consistingof hydrogen, alkyl, alkoxy, cyclohexyl and phenyl and R. stands for a monocyelic NH-B.

radicle of the benzene series, which dyestuffs are easily soluble in water and yield on animal fibers brown shades of good iastness properties.

2. A monoazo dyestufi consisting substantially of a product of the formula:

NHOO on:

.HOIS

which dyestufi represents a dark powder, soluble 'in water, dyeing wool and silk very deep brown shades of good fastness to ironing and of good levelling power. I

3. A monoazo dyestufl. consisting substantially of a product of the formula:

NHOO cm COCH;

RICHARD FLEISCHVHAUER. 

